Diamond Head Oahu

Oahu Vacation Packages

 
Oahu, "The Gathering Place", is home to Honolulu, Hawaii's largest city. Iconic Waikiki dazzles with its classic beaches, exciting nightlife and world-class cusine. On the northen side of the island, the surfer's paradise of North Shore, home of the Banzi pipeline and scenic rainforests offers a laid back island style visitors are sure to enjoy. To the West, Pearl Harbor is steeped in history with its WWII memorials and massive ships. Throughout the island a fusion of asian, polynesian and western culture give Oahu a flavor all its own. Enjoy the best Oahu deals on Hawaii vacation packages today!

Travelers to Hawaii are required to complete a mandatory Safe Travels online travel and health questionnaire no sooner than 24 hours prior to departure. Travelers must self-quarantine for 14 days or for the duration of their stay, whichever is shorter. Those arriving on and after October 15, 2020 who present proof of a negative NAAT COVID-19 test taken no more than 72-hours in advance of arrival are exempt from quarantine.

Hawaii Fall & Winter Getaways
$100 OFF per booking
  • Book by 11/1/20 for travel through 6/30/21
All Deals Include: Round-trip flights, hotel accommodations, taxes and more
  • Aston Waikiki Beach Hotel
    Aston Waikiki Beach Hotel
    Waikiki, Oahu Our 4-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway.

    With breathtaking views of iconic Diamond Head and steps to Waikiki Beach, experience Aloha Spirit with daily activities, regional cuisine and live entertainment at this lively hotel with an urban-Hawaiian vibe.

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  • Hilton Hawaiian Village Waikiki Beach Resort
    Hilton Hawaiian Village Waikiki Beach Resort
    Waikiki, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    Lush grounds, six spectacular pools, a beachfront lagoon, waterfalls and an array of shops and restaurants are all part of the "Village" experience at this expansive resort.

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  • Moana Surfrider, A Westin Resort & Spa
    Moana Surfrider, A Westin Resort & Spa
    Waikiki, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    This legendary resort, "The First Lady of Waikiki," combines turn-of the-century Victorian elegance with modern Westin amenities and luxuries.

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  • Outrigger Waikiki Beach Resort
    Outrigger Waikiki Beach Resort
    Waikiki, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    “Where the Beach Comes Alive” Our extended ohana (family) will discover local beach and surf culture at this hotel on Waikiki Beach.

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  • Outrigger Reef Waikiki Beach Resort
    Outrigger Reef Waikiki Beach Resort
    Waikiki, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    "Sharing the Arts & Culture of Hawaii" This distinctive, refined hotel presents a new vision of hospitality, combining timeless traditions with modern elegance.

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  • Sheraton Princess Kaiulani
    Sheraton Princess Kaiulani
    Waikiki, Oahu Our 3.5-Star classification designates those properties where guests experience an ideal mix of comfortable accommodations and modern amenities. Most of these hotels feature a variety of services, and offer distinguished style and comfort. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    Experience comfort and relaxation in the heart of Waikiki at this hotel while enjoying an exceptional vacation value.

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  • 'Alohilani Resort Waikiki Beach
    'Alohilani Resort Waikiki Beach
    Waikiki, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    Named among the Best Resorts in Hawaii in the 2019 Condé Nast Readers' Choice Awards, This newly renovated family-friendly resort is across from Waikiki Beach within easy walking to nearby shops, restaurants, and attractions.

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  • Aston Waikiki Beach Tower
    Aston Waikiki Beach Tower
    Waikiki, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    Recently renovated, this exclusive condominium resort offers spacious and elegantly furnished with one and two-bedroom suites with fully-equipped chef inspired kitchens, in-room washer/dryer and ocean views directly across from Waikiki Beach.

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  • Waikiki Beachcomber by Outrigger
    Waikiki Beachcomber by Outrigger
    Waikiki, Oahu Our 4.5-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    "An Oasis in the Heart of Waikiki" This brand new lifestyle resort which just completed a $35 million modernization offers contemporary comfort, camaraderie and fun.

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  • The Royal Hawaiian, a Luxury Collection Resort, Waikiki
    The Royal Hawaiian, a Luxury Collection Resort, Waikiki
    Waikiki, Oahu Our 5-Star classification designates those select properties that provide exquisite service and amenities. The discriminating traveler will find the accommodations, ambiance, dining, and staff assistance of the highest caliber. These properties offer the utmost in luxury and will provide an outstanding experience.

    This legendary hotel, known as the Pink Palace of the Pacific, offers a redefined luxury experience.

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  • OHANA Waikiki East by Outrigger
    OHANA Waikiki East by Outrigger
    Waikiki, Oahu Our 3-Star classification designates those properties where guests experience an ideal mix of comfortable accommodations and modern amenities. Most of these hotels feature a variety of services, and offer distinguished style and comfort.

    Discover exceptional value at this family-friendly hotel offering 1- and 2-bedroom suites with kitchenettes in the heart of Waikiki, just five minutes from the beach.

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  • Luana Waikiki Hotel & Suites
    Luana Waikiki Hotel & Suites
    Waikiki, Oahu Our 3.5-Star classification designates those properties where guests experience an ideal mix of comfortable accommodations and modern amenities. Most of these hotels feature a variety of services, and offer distinguished style and comfort. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    This contemporary boutique hotel located just a short stroll to Waikiki Beach offers comfort and value with 1 & 2-bedroom suites with full kitchens in a desirable location on Kalakaua Avenue.

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  • Park Shore Waikiki
    Park Shore Waikiki
    Waikiki, Oahu Our 3-Star classification designates those properties where guests experience an ideal mix of comfortable accommodations and modern amenities. Most of these hotels feature a variety of services, and offer distinguished style and comfort.

    Fronting Waikiki Beach, this hotel features magnificent ocean views and innumerable conveniences.

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Hawaii $100 OFF per booking: Valid on new bookings made 8/31/20 - 11/1/20 for select travel through 6/30/21. Minimum 3-night hotel accommodations at participating property and roundtrip airfare required. Savings is per booking, taken at time of booking and reflected in rates shown.
Rates quoted are per person, based on double occupancy unless otherwise stated. Rates for other travel dates may vary. Rates, terms, conditions and itinerary are subject to availability. Certain restrictions apply. Rates shown include government-imposed fees and taxes. Airline fees for optional services, including, but not limited to, baggage fees, may apply. Airline tickets are non-refundable and subject to airline change/cancellation penalties and rules, including pre-flight notification deadlines. Fees and policies vary among airlines and are subject to change without notice. Please contact the airline directly for details and answers to specific questions you may have. Additional restrictions apply. Advertised rates do not include any applicable daily resort or facility fees payable directly to the hotel operator at check-out; such fee amounts will be advised at the time of booking. Where applicable, kids stay free in same room as adults using existing bedding. Occupancy limits apply. Where applicable, kids eat free with full paying adult. Not responsible for errors or omissions. [Pleasant Holidays acts only as an agent for the various travel providers shown above.]